Ex-Googlers, Stanford professors, and startup CEOs share their best advice on making a career change

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Sebastiaan ter Burg/Flickr

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Samantha Lee/Business Insider

  • Thinking about making a career change?
  • Find out what these experts and executives have to say about quitting your job and searching for a new one.
  • For example, don’t change industry and function at the same time, and don’t wait until you’re doing bad work to leave your current role.

The devil you know is, presumably, better than the devil you don’t. That’s why so many of us stay stuck in a job, an industry, or a lifestyle that’s not working out.

But making a career change doesn’t have to be intimidating. Ask an expert who’s done it (or counseled hundreds of people who’ve done it) and they’ll tell you it’s about breaking down the transition into bite-size pieces and never letting fear be your guide.

Below, we’ve listed practical tips on changing careers, from folks with a range of backgrounds. There’s Julie Sweet, a partner at a law firm who became the CEO of Accenture North America; there’s Paul Ollinger, an early Facebook employee turned comedian; and there are nine other founts of wisdom.

Read on for the knowledge and inspiration you need to reshape your career trajectory.

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SoFi VP and former Facebook exec Libby Leffler: Remember that the career ladder doesn’t exist anymore

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Libby Leffler.
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Steve Maller

Leffler is the vice president of membership at personal finance company SoFi; before that, she worked at Google and Facebook.

She said the career ladder – a predictable series of steps from college graduation to retirement – is all but dead.

Thinking back on her own career trajectory so far, Leffler said: “I wasn’t only focused on the next level up. I was really always drawn to things that intrigued me, gave me the chance to learn as much as I could, and gave me the opportunity to learn something new, with plenty of room for experimentation.”

Leffler added that she never shied away from, say, moving to another team within her company, even if it wasn’t a promotion per se. At Facebook, she started out as a client partner, then became a business lead to the chief operating officer and a strategic partnerships manager.

She advised others to do the same: “Sometimes this means taking that role that might be the same level on a different team, where you can learn a totally new skill, or you can change roles. Then you can level up into something else where you can leverage the new skill you learned.”

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Marketing and strategy consultant Dorie Clark: It’s never too late to transition careers

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Dorie Clark.
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YouTube/Talks at Google

Clark is a marketing and strategy consultant, an adjunct professor of business administration at Duke University’s Fuqua School of Business, and the author of books including “Entrepreneurial You.”

On an episode of the Art of Charm podcast, she explained why transitioning careers when you’re no longer a fresh-faced new college grad doesn’t mean starting from scratch.

In fact, you’ve likely tackled step one: meeting a lot of people, even if they all work in your current industry. Step two is to capitalize on your existing connections to help launch you into your next career phase.

One strategy Clark suggested is “reaching out to friends of yours who are as different from you as possible and saying, ‘Hey, who do you know that I should meet?'” Or, Clark said, if you have some money saved up, you might use those funds to visit an ideas conference and schmooze with fellow attendees from varying backgrounds.

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Early Facebook employee Paul Ollinger: Consider what you would do if you weren’t afraid

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Paul Ollinger.
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Kiki Network

Ollinger worked in sales at Facebook between 2007 and 2011, making him one of the company’s first 250 employees.

Today, he’s an Atlanta-based stand-up comedian and the author of the book “You Should Totally Get an MBA,” a comedic guide for those debating whether to apply to business school.

For the four years that he worked at Facebook, Ollinger saw the same poster every day, with the question, “What would you do if you weren’t afraid?” At some point, he realized his answer was comedy.

In 2014, he made the transition. He said, “I got to a point where I couldn’t not do it, that I had to just say, ‘This is what I’m going to do,’ despite not knowing how I would actually finish a project or knowing whether or not it would be good. I had to be OK to risk bombing at 47 years old in a comedy club.”

Ollinger added, “That’s a pretty insightful guidepost into doing what each of us is supposed to be doing. And if each of us is doing that thing at which we’re the best and/or most passionate, then I think the world is better off.”

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Accenture North America CEO Julie Sweet: Your dreams should scare you

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Julie Sweet.
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Accenture

Sweet is the CEO of Accenture North America. In 2010, she left the law firm Cravath, Swaine and Moore, where she was a partner, to become general counsel for the global consulting firm Accenture.

She told The New York Times that, after 17 years at the law firm, she got a call from a recruiter about the Accenture opportunity.

“I always look back and wonder: Why did I take the call? Why did I take the meeting?” Sweet told The Times. “I had two small kids. I was very successful. I could see my future.”

“It’s about not wanting to be complacent, and wanting to continue to be challenged and learn,” she added. “It’s this idea of, if you can see your future, then you probably are not challenging yourself enough.”

“I have this little plaque that my husband hung on our wall at home,” Sweet told The Times. “It says, ‘If your dreams don’t scare you, they’re not big enough.'”

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Career coach and ex-Googler Jenny Blake: Pivot careers cautiously

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Jenny Blake.
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Mark Hanauer

Blake is a career coach, a former Googler, and the author of “Pivot: The Only Move That Matters Is Your Next One.

She said the best way to make a career change is a four-step process: plant, scan, pilot, launch.

First, you figure out what’s currently working by asking yourself: “What am I insanely good at? When do I feel most ‘in the zone’? What natural talents have I refined into strengths over time?”

Then you scout out “people, skills, and projects that look interesting for this next direction of your career.”

Finally, you run a few experiments to see if your idea is viable until you’re ready to make your move.

Blake said, “By repeating plant, scan, pilot, you reduce risk, but ultimately when it comes time for a launch, whether it’s quitting your job or starting a business, you go all in, even with the remaining uncertainty.”

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Executive coach Erica Keswin: Don’t change industry and function at the same time

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Erica Keswin.
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@telyfoto

Keswin was an executive coach at New York University’s Stern School of Business; now she’s a workplace strategist and the author of “Bring Your Human to Work.”

She said she gives the same piece of advice to all her clients who are looking to shift careers: “It’s very difficult to change industry and function at the same time.”

For example, say you currently hold a finance role in the fashion industry. Keswin recommends that you consider either staying in fashion and moving to the role you’d prefer or staying in a finance role and moving to the industry you’d prefer. Once you have some experience with either a new role or new industry, you can think about making a bigger switch.

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Stanford professors Bill Burnett and Dave Evans: Conduct life design interviews before making any big changes

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Bill Burnett and Dave Evans.
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Michael Lionstar

Burnett and Evans are professors at Stanford and authors of the book “Designing Your Life.” Together, they teach a course at Stanford by the same name as the book.

According to Burnett and Evans, the first step to take when you’re thinking about up-ending your professional life isn’t giving your boss your two weeks’ notice – it’s conducting “life design interviews.”

A life design interview involves asking someone who’s achieved what you hope to achieve to tell you their story. How did they get where they are today and what’s it like to have their job? Their answers to these questions will help determine whether you decide to pursue the same line of work.

All you need to do is invite them out for a cup of coffee for half an hour. (Getting them on the phone would probably work, too.)

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Gusto COO and ex-Googler Lexi Reese: Find the intersection of what you love, what you’re good at, and where there’s a need

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Lexi Reese.
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Colin Price Photography

Reese is the COO of human-resources software company Gusto; she’s previously held management positions at Google and American Express.

Each time Reese thought about making a career move, she asked herself the same questions to reach a decision. “The most fulfilling journeys are ones where people are really honest with what they love, what they’re good at, and where they see a big need,” she said.

As for Reese’s decision to leave Google after eight years, she said: “I loved the purpose of doing [work] to create a world where everybody had access to information [but] I saw myself doing more of the management of the business, as opposed to the building of the business.”

She asked herself: “How do I get back to serving a segment of the world that needs the service?”

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Ex-Netflix exec Patty McCord: You should be doing something you love, you’re skilled at, and your company needs

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Patty McCord.
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Devi Pride

McCord was the chief talent officer at Netflix, and she now runs her own consulting business. She’s also the author of “Powerful: Building a Culture of Freedom and Responsibility.”

McCord presents an algorithm that managers can use to determine whether an employee is a good fit at the company. Individual employees can use the same algorithm to figure out if or when it’s time to move on. Here it is:

Is this what the person loves to do, that they’re extraordinarily good at doing, something we need someone to be great at?

Sometimes, she said, “You could be doing so much more and there’s stuff you’re really passionate about and the company just doesn’t care.”

Other times, “You’ve got a job you can do; you just don’t love it.”

In still other cases, “You work really hard every day and you know it doesn’t matter.”

If any of these scenarios sound familiar, it might be time to leave.

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The Muse exec Toni Thompson: It’s time to quit your job if you’re doing bad work because you’re so frustrated

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Toni Thompson.
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Courtesy of The Muse

Thompson is senior vice president of people and talent at job-search and career-advice site The Muse, and she’s spent more than a decade working in human resources.

According to Thompson, there’s a practical reason to free yourself from the drudgery of showing up at a job you hate: You want to leave on a high note. If it’s gotten to the point where you’ve started doing bad work, it’s almost certainly time to go.

Oftentimes, Thompson said, “you start doing bad work because you are so angry about your situation or are frustrated.”

Here’s why that behavior should concern you. Thompson said you definitely shouldn’t stick around in a job “where you are fully capable, and in the right role, and you were really doing great work” or “you’re suddenly not doing a good job, and you’ve become a bad teammate and a bad employee because you’re so frustrated.”

“At that point,” Thompson said, “it’s probably best to just move on without a job so that they actually have a good memory of you.”

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WayUp CEO and ex-Googler Liz Wessel: When you’re distracted by the prospect of your next step, it’s probably time to move on

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Liz Wessel.
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WayUp

Wessel is the CEO of WayUp, a job platform for college students and early-stage professionals; she previously worked at Google.

“If you can’t do a good job at your job anymore because you’re spending all of your time thinking about another job opportunity, that’s probably a good sign,” she said.

That’s true even if you’re not planning to launch a company. Wessel said of her friends who have made career transitions, “The one thing we had in common was we couldn’t stop thinking about something else,” she said. “Like, ‘I just really want to work at this one tech startup that I’m just so passionate about’ or ‘I’m in finance but I just love this one fintech company.'”

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